Triethylsilane → HCID 77106160, compound

HRID 1053129Notes

Reaction equation

HRID 1053129 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH3:24])[CH:19]=[CH:18]4)[N:14]=2)[N:6]=[N:5]1)([CH3:3])[CH3:2].C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH3:24])[CH2:19][CH2:18]4)[N:14]=2)[N:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 90273484HCID 90273484, compound

Product 1

HCID 77106160HCID 77106160, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-5-(1-methyl-1H-indol-5-yl)-pyrazin-2-ylamine (200 mg, 0.60 mmol) in TFA (10.0 mL) was added triethylsilane (0.19 mL, 1.20 mmol) at 0° C. The reaction temperature was stirred for 2 h at 0° C. The reaction mixture was poured into ice-cold water (20 mL), basified with saturated NaHCO3, extracted with EtOAc (30 mL), dried over anhydrous Na2SO4 and evaporated the solvent under reduced pressure to get crude compound. Crude compound was washed with diethyl ether to afford the title compound as a brown solid.

Workup

  1. extractionextracted with EtOAc (30 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. customevaporated the solvent under reduced pressure
  4. customto get crude compound
  5. washCrude compound was washed with diethyl ether

Sources & evidence

ORD record
ord-96beb38f7dcb4f80aca9174ae8ff3a26
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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